When Puff Daddy was still called Puff Daddy, back in 1997, long before his clothing line Sean John won a CFDA, he was infinitely more ostentatious. To prep for the VMAs, we pick him up at his yacht, where he’s soaking in a hot tub with his son Justin and stepson Quincy. If you’re a fan of My Super Sweet 16, you can gauge how long ago this was by how little and adorable the two are. We squire the three men off in a black stretch limousine to hit the boutiques in search for multiple outfits for Puff, since the rap mogul is feeling himself in a “male Diana Ross” mode: He needs a rehearsal outfit, a red carpet outfit, a performance outfit and a “sitting down in my seat oufit.”

First, we go to Prada, where a collegiate look (slacks, sweater, white shirt and a thick, cumbersome necktie) is deemed too preppy. Puff opts for a brown leather car coat instead. At Gucci, he picks up some logo hardware loafers and mentions that he likes an element of Elton John and Liberace in his style. He enjoys logos on his clothes, despite the tackiness. A dark blue, shiny shirt is also copped because it looks good against the moon man. A jet-black suit, double-breasted but with a concealed placket, is also purchased.

At Versace, Puff swoons over a suede suit with a long jacket, and notes how beautifully the Italian house’s garments always fit.

It’s interesting that this was the heyday of conspicuous consumption in rap, as lyrics shifted to include Italian and Parisian fashion brand names. It was also the beginning of the "Shiny Suit" era, which Puff, Ma$e and Hype Williams set off with the “Mo Money Mo Problems” video, styled by June Ambrose. Originally, the director wanted leather suits, but June won, and the ensembles that spawned a thousand glinting replicas were born. “With the metallic suit, it was [convincing] Puffy, this hip-hop artist, that this was going to be impactful,” she says. “I showed him the red metallic and he says, ‘I am not wearing that. I was like, ‘Please trust me.’ I had to make one red leather outfit and one metallic leather outfit and… I won!”

Blessedly, Diddy has since grown partial to classic tuxedos, narrow lapel suits, cashmere sweaters, black tees, and varsity jackets, with only the occasional sparks of flamboyance in his flashy outerwear — no more reflective clothing or oversized dyed leather jackets.